Should You Buy a Holiday Gift for Your Boss?

2017 Update: We still stand by this advice on gifts for bosses, but you may also want to check out all of our posts on holiday business etiquette.

Should you get presents for your boss? If so, what gifts should you get? Reader A wonders:

I’ve been with my company for less than a year, and it’s also my first corporate job. I work in a very small team, consisting of my two bosses and myself. As holiday season is almost upon us, I was wondering if you had any guidelines for what (if anything) is appropriate to give as a small gift for two supervisors who have been very generous with their time and expertise while I’ve been learning the ropes. Any suggestions welcome!

Hmmn. Hmmmn. We’ve talked about gifts for associates who refer you new business, hostess gifts for a dinner party at your boss’s house, and gifts for your secretary, but this is a new one, and I’m curious to hear what readers say. For my $.02: I would be verrrry careful about giving gifts to a boss because I think it’s unnecessary, and it’s easy to offend. A too-personal gift (like towels or something) may create the impression that you don’t know the difference between family and the office. On the other hand, a too-impersonal gift (a random gift that reads “this is my go-to gift when I don’t know what to get,” like a bottle of wine or a box of fruit) simultaneously smacks of “why even bother” along with “wait, does she think we were supposed to get her something?” A gift that’s too small (like a $25 gift card) is both cheap and insulting (as in, you think your boss needs a $25 gift card) — but a gift that’s too generous raises the problematic interpretation of, “she isn’t working for the money.”

So here’s my $.02: don’t get them anything. If you must, though, here’s my suggestion: get something small but thoughtful that relates to something your boss told you in the course of your conversations. Note that all of the above disparaging comments on towels, wine, pears, and gift cards go out the door if your boss avidly collects towels (or always carries one with him) or whatnot. Things to convey with your present:

I listen well and pay attention to details!

I appreciate what you’ve done for me this year!

The gift is a gesture and isn’t a big deal.

If at all possible, I’d try to avoid the impression that you scoured the ends of the earth to find the perfect gift for your boss — rather, serendipity placed the perfect gift in your way and, well, you just HAD to get it after that conversation that time about the thing.

Maybe I’m crazy? Would you get your boss anything? If yes, what would you get for a boss in a small office? What message(s) would you want to convey?

Comments

When I was in law school I worked for a (locally) well known firm. All the clerks were warned in advance that Christmas was a lavish affair and to prepare accordingly. I had no idea what to expect – I was out of town for the firm party (snowed in elsewhere) but I was given a large amount of money in gift cards from my bosses. I was told to only get gifts for my immediate boss. I gave him a Burberry tie, which seemed to fit the bill of “don’t be cheap” but also was impersonal/not inappropriate.

I now work in corporate America, every year the bosses bake cookies for the team and some people exchange cards (no gifts).

I work in a VERY small NYC firm with onley 15 attorney’s and we HAVE to play secret Santa. Yay! I love Secret Santa!

Also, even tho we do NOT have to, I ALWAYS give my boss, the manageing partner, a special extra gift each year, b/c he sponsored me for my clotheing allowance. I limit the value to $100 or less, so it is NOT extravegent. I watch all year to see what it is he need’s then I get it. This year, I see that his wallet is all ratty, so I have my eye on a nice Coach or Michael Kors wallet for him. I will put in the difference between what I pay and $100 so that he know’s what I am doing for him. It is all in the spirit of the holiday, like Secret Santa.

Last year, I had to get something for Lynn b/c I was HER secret Santa, and I got a nice Victoria Secret teddie for her b/c I knew she and Mason were playing house, so it would come in VERY handy. Mason was walkeing around tired for week’s after the holiday. On the other hand, Bill, one of the older attorney’s was MY secret Santa, and he got me some cheep perfume from Dwayne Read (a local NYC drug store). That is the kind of cheep stuff Alan (my ex) used to get for me–I will never figure that out b/c he knew I would NOT wear it, so I gave it back and he probabley gave it to his younger sister. Men are rediculeous some times, but we women know that and have to put up with it. FOOEY!

Do you have any peers to ask for guidance on this? At my office, no one gifts up. Too awkward for the reasons mentioned in the post. I think a thoughtful message on a holiday card, no gift, would be the best solution here.

This is what I was going to suggest, this can vary so much from office to office. At Old Job, we got our boss a fairly big gift (think spa gift card) with each of her direct reports contributing. At this job, we do a group gift but it’s much more low-key (I think last year we got her a six-pack of mixed beers). And I know at some places, it would be very odd to get a gift for your boss. I know etiquette says gifts should never go up, but I think it’s nice to recognize a boss who works hard and tries to make the workplace a pleasant one.

I would not purchase a gift for my boss unless we were real life friends outside of work. Otherwise, as Cat said, a thoughtful message on a holiday card (note “holiday card” and NOT “Christmas card”) should suffice.

I’ve had good luck making pretty little food gifts (chocolate-dipped chips in plastic gift bags was the favorite) for everyone in my department. Nothing super fussy, and I don’t bother with baking. This is after seeing there was a tradition of everyone doing holiday cards and bosses giving gift cards to supervisees.

I second this – instead of a gift card or any gift with monetary value, it’s best to prepare a small gift bag with chocolates and a card or something. I’ve had coworkers who have given to all their coworkers and immediate managers pretty mini gift bags with the large Ghirardelli squares, and a tiny card – it’s enough to convey the spirit of the holidays without getting into the awkwardness of figuring out what to gift up.

Awkward Gifting: Many years ago when I was young and dumb, I made killer jelly from a red currant bush at my house. I brought in gaily wrapped jelly for those work girlfriends (and one guy whose wife and I were friends) who were at my level or slightly lower. Misogynist Senior VP two levels above me – who had previously made bad jokes about [email protected] at a corporate event, at which I was the only new mother – asked why he didn’t get any jelly. So I had an extra and gave him one. It sat on his shelf for a few weeks and then I’m sure it was trashed. Never got thanked. If I had it to do over, I’d say “Sorry it was a limited batch.”

In SP’s defense, people who are watching their weight / counting calories sometimes have to toss well-meant gifts of fattening food. Your cookies probably are awesome, and SP should have been more discreet, but I seldom have calories for stuff like that, so I feel her/him.

I agree! Two supervisors who worked for me gave me home made fudge and peanut butter balls every year…I try to not go overboard on sweets, and they have to be super duper. These weren’t. I’d thank them but take them home and throw them out.

I think this really depends on the workplace. I agree with the rule generally but at my small firm, the partners get gifts from all the associates so if you don’t participate, it reflects poorly on you. I keep it small (chocolate or wine generally) with a card.

Our team is always struggling to keep our corporate iPhone charged. I am going to get my boss and peers portable iPhone batteries to keep in their briefcases. I figure it’s relevant and reasonable in price.

OK, I have a related question. I clerked for a judge who has a little holiday party every year for her past clerks and friends of the court. Everyone brings her something, but most people resort to the old bottle of wine route. So, she’s not my boss (my clerkship was only a year and I do not practice in her court) but she’s still in a boss type position. Any suggestions on gifts?

This is totally, 100%, know your office. My team does a group gift for our boss. We all contribute $20 and get him something nice. He throws a pretty generous department holiday party for us and is one of the most laid back down to earth guys you could work for–we all adore him. It sounds inappropriate to most people on this board, but here it makes sense.

If I was working anywhere else, I would not gift up. Just be cheerful and do good work. Maaaaaybe a bottle of wine if it makes sense, but not more than that.

I would say the opposite, do not get something too thoughtful for your boss. A generic gift everyone likes like alcohol or chocolate seems more appropriate, if you must. It seems overly personal to try to get some thoughtful gift. I think I may be creeped out if someone were to get me, like, that pair of earrings I’ve been coveting or a class pass at my local yoga studio a signed copy of my favorite book or whatever. Overstepping! Unless you mean something like getting your boss a blue pen because they like the color blue.

What about lateral gifting? The tradition here is for the partners (6 of us) to gift to each other. It has been things like hand thrown mugs, movie gift cards, bottle of wine, etc. I feel it is unnecessary and slightly awkward but as the newest partner I can’t really say I’d rather not participate.

Ask a Manager says gifts should only flow “down” in the workplace…and I agree. I’m an associate and have never gotten my bosses (partners) a gift, only secretaries/paralegals. A few of my bosses have gotten me small gifts (i.e. $10 starbucks card) which I appreciated the gesture but did not expect.

Ugh, this is such a stressful question. The culture at my firm (15 lawyers) is that the associates get partners gifts. All of my partners are men, so last year I knocked it out of the park by finding a whiskey distributor that would engrave a bottle of their whiskey for free if you bought the bottle and dropped it off. Found cool lawyer quotes and had them engraved with the partner’s name. Totally stumped on what to do this year though.

I recommend looking through the archives of Ask A Manager for advice on this question. I think the general feeling is that gifts should not flow ‘upward’ to your boss in a working relationship. If you want to acknowledge their help and support over the last year, write a heartfelt note in a holiday card thanking them for what they’ve done. It will probably mean more to them than a token gift will.

Year one I gave my bosses games that their kids would enjoy. They said their kids loved them. Year two our office all went in on personalized mugs with the firm name. Year three everyone went in on mouse pads with some of the bosses favorite expressions/sayings.

I work in a small department with 3 other attorneys, one of whom is our boss. We have a very collegial work environment and enjoy each other’s company.

Last year, we opted to treat her to a nice happy hour at an upscale restaurant. It worked perfectly – we spent about the same as we would have on gifts, but it was a much more memorable experience. We’re planning a similar evening this year.

I think this is TOTaLLY know-your-boss. I had a boss that was a true mentor to me. She got (and still gets!) a card from me, usually with a personal but token gift (she loved opera, cooking,boating, theatre…there were many option!). I also drove across the state once to see her in a community play she was doing ;)

My current boss is more like a friend/boss. She’s the SVP of our company but is still my FB friend, drinking buddy, etc. We came up through the company together and have worked with/around each other for a long time. Iwork more “with” than “for” her; she just signs my paychecks. I get her a bottle of wine I know she will like with a “looking forward to another great year.”

I think there’s safety in numbers. We initiated a quarterly birthday party for our little workgroup which includes the director. We all pitched in an equal amount and at the party (at a restaurant), I asked CFO to grab the check so our boss didn’t pay. He wasn’t fast enough… Boss still paid for his own birthday party…
That being said, I agree that in general gifting up is too awkward and fraught with peril.
I think the suggestion of something small and thoughtful works, though. Like a puppy teething ring for a new puppy in the home after you’ve seen the “awwww!” pictures and heard she is chewing and biting (teething symptoms).

So what’s the best policy for gifting “down”? I’ve got a team of 12 working for me and I’m stumped. Starbucks cards feel too impersonal, homemade treats too personal, gift baskets over the top, since heymre spread to different sites. What are some of the favorites folks have received from your bosses?

I work at a mid-size firm, in an office of about 40 attorneys. I bake every year for Christmas gifts for friends, and each year I give the 4-5 main partners that I work for something like a small wrapped package of homemade cookies, or a mini-cake. They always seem to appreciate it (and often eat the present that very day), and it never seems awkward. I usually give my mentor a nicer gift, like a bottle of wine, but that’s because she is also my friend.

This year, I’ve been working more with the managing partner of our office, and he’s really taken me under his wing and has been mentoring me in the industry he specializes in. I’m incredibly grateful, and it is a great and invaluable thing for my career. Even though I’ve done work for him before, I’ve never given him a gift. Maybe this is a stupid question, but for me, it seems more awkward to give the managing partner something than it seems to be to give the other partners a little something. Should I include him this year? Or leave things as-is?

Last year I got my boss a little box of artisanal (I hate that word–but that is what these were) chocolates from the local holiday market. Real chocolate is infinitely better than the cheap stuff and unlike other sweets at holiday time keeps for much longer. Plus it was not extravagant enough to make anyone uncomfortable.

Definitely a know-your-office kind of thing. We always exchanged gifts with our boss, and they were of equal value…just a small gift. I think I got her a Fresh lip balm set one year because I knew she loved the Maybelline Baby Lips tinted balms.